A top-notch fielder, Kiki "Don't Call me Shirley" Cuyler played for the pennant-winning Pirates in 1925 and 1927. He later moved to the Chicago Cubs, where he played from 1928 to 1935. In 1929 and in 1932, he got to play for two more pennant winners, though the Cubs lost to the Athletics in 1929 and the Yankees again in 1932.
A career .321 hitter, he was also one of the National League's outstanding outfielders of his day. He batted .300 in 10 of his 15 seasons as a regular, topping .350 four times. Four times he led the circuit in stolen bases as he played for four pennant winners. His seventh game, eighth inning, bases loaded double off Walter Johnson won the 1925 World Series for the Pirates.
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